Extension Candidates Rumors

The Pirates have recently been amongst the game’s most aggressive teams in pursuing early-career extensions. Since taking the GM seat in Pittsburgh back in the fall of 2007, Neal Huntington has locked up deals with ten players for a total of 37 years and $182.9MM. Only two of those contracts went to players with four or more years of service.

Among the team’s most recent efforts were successful pacts with star outfielders Andrew McCutchen (six years, $51.5MM) and Starling Marte (six years, $31MM), with the former inking with 2.123 years of service and the latter signing with just 1.070 years to his credit. While those deals haven’t all been successful — neither Jose Tabata nor Nate McLouth, for instance, delivered value on their deals, though neither did they hamstring the club — the aggregate benefit to the organization is undeniable.

Pittsburgh, riding high on two straight postseason appearances, spent a relatively large amount through free agency this last offseason and seems in good position to stay competitive for years to come. The team has continued to explore ways to add value to its player assets through extensions: in particular, it made a long-term offer to then-untested outfielder Gregory Polanco last year, though those negotiations seemingly stalled. In spite of their relatively meager spending capacity, the Pirates appear to have plenty of future flexibility, with less than $12MM on the books for 2018 and even less thereafter.

While another run at Polanco obviously remains possible, it is fair to wonder whether the team might turn its sights elsewhere this spring. Josh Harrison remains an intriguing possibility, as MLBTR’s Steve Adams discussed last fall. Beyond that, there is one obvious potential candidate who brings immense upside — and, given the nature of his craft, risk: young ace Gerrit Cole.

Cole, 24, has done exactly what the Bucs hoped when they made him the first overall pick in the 2011 draft, reaching the bigs in 2013 and establishing himself as a quality starter off the bat. To date, he has thrown 255 1/3 big league innings with a 3.45 ERA and 8.4 K/9 against 2.4 BB/9. Advanced metrics suggest he’s been even better, as he owns a career 3.09 FIP, 3.20 xFIP, and 3.28 SIERA. Cole consistently works in the mid-90s with his fastball and has averaged a strong 49.1% groundball rate thus far. Needless to say, the outlook is positive.

If there is one red flag on Cole, it is health. First and foremost, he is a pitcher; as we are constantly reminded, any arm is at risk of injury at any time. But there is some additional cause for concern in his case, as Cole missed significant time last year owing to shoulder issues. He returned and posted good results late in the season, and does not have any significant history of problems prior to 2014. And he has reportedly worked to smooth out his mechanics and incorporated exercises to maintain his shoulder health.

With just 1.111 years of service to his name entering the 2015 season, Cole will not qualify as a Super Two and is set to hit arbitration eligibility in 2017. That means he will not reach free agency until 2020. Despite his rapid ascent to the bigs, Cole will reach the open market at age 29 — still relatively young, but not as early as some quick-to-the-bigs phenoms. Those factors, along with the risk of injury and performance, generally transfer significant leverage to a team, of course.

In this case, though, there are some significant offsetting considerations. For one, Cole was signed to an $8MM deal out of college, meaning he has already secured life-changing money. For another, he is represented by agent Scott Boras. Contrary to popular opinion, Boras has overseen pre-free agent deals for his clients, many of those contracts have not sacrificed free agent seasons. And, on balance, he certainly carries a deserved reputation for bringing his players onto the open market in search of huge paydays.

To be sure, it is far from a sure thing that Cole would be receptive to contract talks at this stage. If he is, however, both sides will have plenty of precedent to work from. Looking in at recent extensions for starters with between one and two years of service, one finds a host of comparables. First on the list has to be Madison Bumgarner, who got five years and $35MM from the Giants while giving up two option years back in 2012. More recently, Julio Teheran and the Braves linked up on a six-year, $32.4MM deal that conveyed one option year to Atlanta.

The Bumgarner comp, in particular, appears to be a good one; indeed, he was perhaps slightly more accomplished — and significantly younger — at a similar point in his service timeline, and had already put up a fully healthy season of over 200 frames. Teheran signed before his age-23 season, coming off of a 185 2/3 inning season of the sort that Cole has yet to accomplish. Cole’s representatives would no doubt point to the $200MM+ contracts that have been given to free agent starters in recent years as evidence of salary growth, though Cole’s shoulder concerns and additional age would serve as counterpoints. While it is, perhaps, possible to argue that Cole possesses greater upside than Teheran, or at least more than he did at the time his deal was struck, projection systems seem to hold the two righties in approximately the same regard heading into 2015.

What is most interesting about Cole’s situation, perhaps, is what it could theoretically tell us about where pre-arb extensions are headed. Somewhat unlike other areas of the market, early-career pitching extensions have not exhibited much growth. In addition to the Bumgarner and Teheran examples, which came two years apart, extensions for pitchers with between two and three years of service have largely followed a script for some time: Gio Gonzalez (five years, $42MM, two options) holds the record in that class, but Chris Sale‘s 2013 deal (five years, $32.5MM, two options) was not substantially different from, say, the 2011 Trevor Cahill contract (five years, $30.5MM, two options).

As I explained in breaking down last year’s notable Freddie Freeman extension, and as the Mike Trout and Giancarlo Stanton extensions further demonstrate, the position player extension market has seemingly broken out of any molds. On the pitching side, the most significant recent deals have gone to players on the verge of free agency (Clayton Kershaw and Homer Bailey, for instance). Locking up Cole could require a market-resetting deal; it remains to be seen, of course, whether either team or player are willing to make that happen.

Since arriving from the Athletics organization in a seemingly minor trade following the 2012 season, starting pitcher Tyson Ross has blossomed in San Diego. He followed a strong 2013 with a terrific 2014 campaign in which he posted a 2.81 ERA, 9.0 K/9 and 3.3 BB/9, with his only obvious blemish coming when he missed his last start due to a slight forearm strain. Ross looks like a starting pitcher the Padres can build around, and at least for now, the Padres seem to agree, declining to trade Ross and Andrew Cashner even though new GM A.J. Preller used the trade market to transform much of the rest of the team this winter.

Ross posted a 1.88 ERA in the pitcher’s haven of PETCO Park and a 3.79 ERA elsewhere in 2014, but he seems like the sort of pitcher who should be able to succeed in any home ballpark. His strikeout and walk totals are strong, and his 56.2 ground ball percentage over the past two seasons is outstanding, ranking third among pitchers who have thrown at least 300 innings in that time. He also has a mid-90s fastball, although he’s relied on that less in recent years, turning instead to a sinker and a ridiculous slider that help generate all those ground balls. If anything, his exceptional ground ball abilities are somewhat wasted in the dead air of PETCO Park.

The Padres control Ross’ rights through the 2017 season, and already the Wasserman Media Group client has established a fairly high salary baseline as a Super Two player. Ross and the Padres settled for $5.25MM this winter for 2015, his second year of arbitration eligibility. That could put him on pace to make about $25MM from 2015 through 2017, depending on how he performs in the next two seasons.

There haven’t been many recent extensions for pitchers with arbitration situations similar to Ross’. Perhaps the one that comes closest is that of Gio Gonzalez, who signed a five-year, $42MM deal with a team option and a player/vesting option three years ago. At the time of that deal, Gonzalez, also a Super Two player, was heading into his first season of arbitration eligibility, with MLBTR projecting a $4.2MM salary for that year. Ross is one year closer to free agency than Gonzalez was, and salaries have escalated throughout the game since then, so the Padres would likely have to pay more heavily than the Nationals. But a deal for Ross in the $55MM-$60MM range with a structure similar to the Gonzalez contract would seem fair. The end result might look something like Matt Harrison‘s current five-year, $55MM deal with the Rangers, which includes one club option.

If Ross has interest in a long-term contract, the circumstances would seem favorable for the Padres to sign him. San Diego has a lucrative new TV deal, and the Padres’ new ownership and seems intent on spending. And while the team has a fairly strong rotation now, they might not have one forever. Ian Kennedy is eligible for free agency after the season, and Cashner after 2016. Even with young or relatively young arms like Odrisamer Despaigne, Robbie Erlin, Matt Wisler and Casey Kelly in the system, signing at least one of Kennedy, Cashner or Ross would seem prudent — the pitcher who remains with the Padres long-term could join James Shields as a veteran rotation anchor.

Of course, with Preller, one never knows. It wasn’t he who traded for Ross, and he hasn’t yet shown strong attachments to players he didn’t acquire. (And he already traded Tyson’s brother Joe to the Nationals in the Wil Myers deal.) Preller could have his mind on something else entirely, particularly given the strong group of starting pitchers available on the free-agent market next winter. There are reasons to be somewhat cautious of Ross, too — he pitched about 60 more innings in 2014 than he did the previous year, and he has unusual mechanics and relies heavily on his slider. All those factors could make him an injury risk. But there’s little else to dislike about him, and if the Padres are comfortable with his health, perhaps the two sides can strike a deal at some point.

Over the last two seasons, Josh Donaldson has quietly been one of the best players in baseball, finishing third in fWAR among position players in the last two years, behind only Mike Trout and Andrew McCutchen. That doesn’t mean, however, that his new team, the Blue Jays, should rush to sign the MVP Sports Group client long-term.

As a Super Two player, Donaldson’s salaries through 2018 will be determined by the arbitration process, and the Blue Jays’ victory over Donaldson in his first arbitration case this winter was a crucial one. Not only was there a significant gap between the number Donaldson camp proposed ($5.75MM) and the Blue Jays’ proposed figure ($4.3MM), but the arbitator’s decision in favor of the Blue Jays will affect not only Donaldson’s 2015 salary, but his salaries from 2016 through 2018 as well.

Donaldson’s statistical profile (offensive numbers that are very good but not obviously spectacular, combined with superb defense) likely made him somewhat underpaid this time through the arbitration process. That effect might wear off somewhat in coming seasons as he moves to a much more homer-friendly ballpark in Toronto than the one he had in Oakland — he hit .255/.342/.456 with 29 homers and 98 RBIs in 2014, and bumping those numbers up somewhat would help him as he enters arbitration for a second time. Still, Sportsnet.ca’s Ben Nicholson-Smith tweeted that a source estimated Donaldson’s arbitration loss this winter might cost him a full $6MM over the next three years. That guess might, if anything, be low.

On top of that, the Blue Jays already control Donaldson throughout what could well be the rest of his prime. Since he got off to a late start to his big-league career, he won’t be eligible for free agency until after his age-32 season. Any extension beyond that would only buy out seasons beginning with age 33. In other words, the Blue Jays have a very good situation with Donaldson, and they have little reason to press their luck with an extension unless it’s a very favorable one. Donaldson isn’t a 23-year-old superstar who figures to be in his prime in his first free agent seasons. He’s a 29-year-old superstar who’s very likely in his prime right now.

If the two sides were to begin discussing a deal, finding a close comparable for a Super Two player like Donaldson would be difficult. We can begin, however, with his likely arbitration salaries through 2018, which might total somewhere around $35MM-$40MM if he maintains impressive offensive totals. Donaldson’s camp could point to Kyle Seager‘s recent seven-year, $100MM extension as a possible model for a Donaldson deal, and that wouldn’t be entirely unreasonable, given that Seager’s deal began in what would have been his first year of arbitration salary, and with a salary of $4MM (although Seager, not being a Super Two player, was a year closer to free agency than Donaldson is). For the reasons mentioned above, though, that seems like a lot of risk for the Blue Jays to assume.

The Blue Jays, then, could hypothetically look at recent deals for Jason Kipnis and Matt Carpenter that each guaranteed about $52MM for six years. Both those deals occurred when the players had between two and three years of service time, but neither Kipnis nor Carpenter were Super Two players, so their arbitration years would likely have been less lucrative than Donaldson’s figure to be. That would likely mean that a Donaldson extension would either require a somewhat higher total, or give away fewer years of free agency.

Perhaps something along those lines could work, although it might be hard to find an equilibrium where the Jays felt like they were taking on an appropriate amount of risk and Donaldson’s camp felt like he was getting a large enough total to forgo free agency following the 2018 season, which might be his only attempt at a significant free-agent payday. Then there’s the fact that Donaldson and the Jays already went to an arbitration hearing — hearings can be tough for some players to take, and could make future extension talks difficult. As Braves assistant GM John Coppolella recently told MLBTR’s Steve Adams, “If you look at the history of players who have gone to arbitration hearings, for whatever reason, very few remain with the same team for the long term. I don’t think the hearings are contentious per se, but the process isn’t exactly friendly and heartwarming.”

If Donaldson and the Blue Jays were to have interest in an extension, then, it wouldn’t be impossible to negotiate one, but it would be tricky. And given Donaldson’s age and years of control remaining, the Jays shouldn’t have much urgency to negotiate a deal.

With his youth, solid performance, strong health record and history of eating innings, righty Chris Tillman certainly seems like the kind of player who ordinarily would get extension consideration. It comes as no surprise, then, that the Orioles are interested in extending the Beverly Hills Sports Council client. It doesn’t sound like discussions have gotten very far, however, and it’s not clear where they’ll end up once they do.

Tillman has pitched over 200 innings in each of the last two seasons, establishing himself as a workhorse at the relatively tender age of 26. After struggling through half-seasons in the big leagues in 2010 and 2011, he’s gotten above-average results. What’s not immediately obvious, however, is why he’s gotten those results. Tillman’s K/BB numbers (6.5 K/9 and 2.9 BB/9 in 2014; 6.8 K/9 and 3.0 BB/9 for his career) are fine but nothing special, and he also isn’t a ground ball pitcher. He’s posted very low BABIPs (.221, .269 and .267) in each of the last three seasons, and he’s stranded runners at a very high rate in each of the last two. Unsurprisingly, Tillman’s xFIP and SIERA figures have run well behind in his ERAs in each of those years, suggesting a back-of-the-rotation type who looks better than he is thanks to the Orioles’ excellent defense. His velocity has also dropped in each of the past two seasons.

Tillman does benefit from the fact that it’s nearly impossible to steal bases against him, however, which doesn’t turn up in peripheral numbers. Also, it’s possible he turned a corner at some point last season — he posted a 4.11 ERA in the first half, then a 2.33 in the second half, with 7.7 K/9 and 1.8 BB/9. That kind of decisive improvement might be mostly variance (Tillman also pitched significantly better in the second half in 2013, but didn’t carry that improvement into the first half of 2014), but it’s also possible he simply got better as the season went on, particularly given his age. Tillman changed his release point as 2014 progressed, perhaps suggesting that at least a portion of his improvement is sustainable. And even if Tillman reverts to his career norms next year, his ability to soak up innings has value. Exactly how good Tillman is can be debated, but if he keeps pitching 200 innings a season, extending him has limited downside (at least by the standards of multi-year pitcher contracts) even if he’s merely average.

It’s difficult to find precedents for a Tillman extension that don’t come with significant caveats. Tillman has between three and four years of service time, and via MLBTR’s Extension Tracker, most recent extensions for starting pitchers with that much service are either very short (two years each for Mat Latos and Clayton Kershaw, for example) or out of date (Johnny Cueto got a four-year deal plus an option prior to the 2011 season, while Ervin Santana got four plus an option two years before that). A long-term deal for Tillman would potentially recalibrate the market for pitchers with similar service time.

So to map out a Tillman extension, we’ll begin with his likely salary heading into his first year of arbitration. Matt Swartz’s model for MLBTR projects that Tillman will get $5.4MM in his first arbitration season, but as Swartz noted last week, that figure is probably unlikely. The current record for a one-year deal for a pitcher eligible for arbitration for the first time is $4.35MM, and Swartz thinks Tillman would approach or match that figure rather than crashing through it.

If Tillman were to make $4.35MM next year, that would still set him up to clear $20MM in his arbitration seasons, depending on his development. If Tillman’s contract were to match the Cueto and Santana deals in structure (four years plus an option), that would put him between $32MM and $40MM. That figure seems low, given more recent extensions for pitchers with slightly less service time, like Chris Sale (who had between two and three years of service time when he got $32MM guaranteed for five years, plus two options) and Derek Holland (who had roughly the same service time as Sale and got $28.5MM guaranteed for a five-year deal with two options). Julio Teheran signed for six years and $32.4MM last offseason despite having just over a year of big league service.

Of course, Tillman and the Orioles could aim longer. For five years guaranteed, Tillman could perhaps ask for the five years and $55MM given to Matt Harrison, who had a year more service at the time of his extension than Tillman has now. Phil Hughes‘ recent deal gave up three years of free agency eligibility at $14MM per season, and a five-year deal for Tillman would give up two. Given what Tillman is set to make in arbitration, a $55MM total, or perhaps a bit less, for the next five years makes sense. Alternately, the two sides could strike a two- or three-year deal, although that would likely be done purely on Tillman’s arbitration projections and probably wouldn’t contain any options.

Given the money Tillman is already set to make in arbitration, it would be hard to blame him for aiming high in extension discussions. The question is whether the Orioles would want to pay $50MM or more for a pitcher with so many sabermetric question marks. If a large percentage of Tillman’s success is due to the Orioles’ defense, it doesn’t make sense for the Orioles to pay a premium for him going forward. Unless Tillman is willing to take a substantial discount, the Orioles’ best route might be to take him year-to-year.

New Cardinals outfielder Jason Heyward only has one season remaining before free agency, and St. Louis likely has the financial flexibility to sign him long term. It’s not surprising, then, that there’s been some discussion in the St. Louis media about the possibility that the Cardinals would extend him. For the right price, Heyward (who’s already set to make $8.3MM in 2015) would be an exceptionally strong extension candidate.

Heyward won’t turn 26 until next August, and he has an excellent all-around game that includes plus defense to go with good on-base ability, reasonable power and above-average baserunning. He might also be able to retain his value as his defense declines, too — his control over the strike zone and toolsy profile suggest he might still have headroom as a hitter.

Of course, the same factors that make Heyward a good extension candidate would also make the Casey Close client a very attractive free agent. The fact that free agency is so near makes an extension a different proposition than it was when MLBTR’s Tim Dierkes examined Heyward’s candidacy early in the 2013 season.

Perhaps the best precedents for an extension for a top position player with between five and six years of service time are those of Matt Kemp (eight years, $160MM) and Adrian Gonzalez (seven years, $154MM). Heyward isn’t, or isn’t yet, the offensive player that Kemp or Gonzalez were — Kemp was coming off a .324/.399/.586 season at the time of his extension, while Gonzalez had just hit .298/.393/.511 in pitcher-friendly San Diego. But average salaries have skyrocketed throughout the game since those contracts were signed in 2011 (the average MLB salary jumped 12 percent just last year), and we should expect extensions to keep pace.

Also, Heyward is two years younger than Kemp was and more than three years younger than Gonzalez at the times of their contracts, a significant matter when the contract would begin with the player heading into his age-25 season (or age-26, depending on how one wants to look at it) rather than his age-27 season (Kemp) or age-29 season (Gonzalez). And Heyward is a far better defensive player than either Kemp or Gonzalez, with a UZR of 24.1 last season and of at least 12 for three seasons straight. Historically, that’s not an attribute that figures to get Heyward paid like huge power numbers would, but it makes it that less likely that his next contract will be a bust — Heyward’s on-base ability and excellent defense significantly limit his downside.

Jacoby Ellsbury‘s seven-year, $153MM deal with the Yankees, signed as a free agent after the 2013 season, provides a recent precedent for a contract for a star-caliber, left-handed outfielder with defensive value. Again, though, Heyward is far younger than Ellsbury, an enormous point in his favor.

Given Heyward’s youth, it isn’t hard to see an extension heading toward at least eight years rather than seven — a nine-year extension would only go through his age-33 season, and even a deal of ten years or more doesn’t seem ridiculous. Heyward isn’t likely to reach the same stratospheric heights as Giancarlo Stanton ($325MM) or Miguel Cabrera ($248MM), but those head-spinning deals should help keep the market trending upward, and it isn’t hard to see Heyward clearing $200MM, as Fangraphs’ Dave Cameron proposed last month. Heyward could also seek an opt-out clause, like Stanton, and like fellow Close clients Zack Greinke, Clayton Kershaw and Masahiro Tanaka.

Or maybe the idea that Heyward is a $200MM player after a .271/.351/.384 season simply won’t add up, regardless of his youth and defense. But perhaps, from Heyward’s perspective, not matching the Stanton or Cabrera deals doesn’t mean he can’t come out ahead in the end. Heyward is so young that he could play his way through a nine-figure extension and still be young enough to land another.

Seen from that angle, a shorter deal, perhaps modeled on Mike Trout‘s six-year, $144MM contract, might make sense. Heyward isn’t as young or as good as Trout, but he might be able to land only a similar total over six years because Trout’s contract began with three pre-free-agency seasons and Heyward’s would only begin with one. That way, Heyward could hit free agency heading into his age-31 season, at which point he would still be young enough to hit it big. A nine-year deal, say, would be much more lucrative, but would probably leave him too old to net another huge contract after it’s over.

That route is probably unlikely, however. Heyward is only one year from free agency and has little reason to give the Cardinals a discount, and he was not particularly motivated to sign an extension with the Braves. That might suggest Heyward could either sign a huge deal for eight-plus years, or hope for a big season, test the free agent market and perhaps wind up with a contract that’s even longer. When you’re as young and as good as Heyward, there are few bad choices.

Asked to create a list of candidates for the 2014 NL batting title five months ago, few would have seriously suggested Pirates utilityman Josh Harrison. However, it’s September 11th, and the .318 mark that Harrison carried into the day paced the National League. A decline in performance for Pedro Alvarez and an eventual season-ending injury for the slugging third baseman have opened the door for Harrison to serve as the club’s everyday option at the hot corner down the stretch — an opportunity on which he has capitalized. Though the 27-year-old Harrison had never even topped 276 plate appearances prior to this season, he’s tallied 472 and should finish the season well north of 500.

The Pirates acquired Harrison with little fanfare in the 2009 trade that sent Tom Gorzelanny and John Grabow to the Cubs and watched him produce steady batting average and on-base percentage marks as he ascended the minor league ranks. However, while his glovework graded out favorably heading into the season, he also carried a career slash line of just .250/.282/.367 into 2014.

Harrison hasn’t drastically changed his approach at the plate — his swing and contact rates are similar to his previous marks — but he’s slightly increased his walk rate, cut down on his pop-ups and laced line drives at a career-high rate. On top of that, Harrison has found some power despite never hitting more than six homers in a minor league season. He’s swatted 13 long balls and posted a .196 isolated power mark even though he plays at PNC Park, which is known to significantly diminish right-handed pop. The end result has been an outstanding .318/.351/.514 batting line to go along with those 13 homers, 17 steals and strong defensive marks.

Harrison has cleared three years of Major League service time now and will be eligible for arbitration this offseason. Clearly, an NL batting title, 15 or so homers and 20 or so steals will help his agents at Millennium Sports Management make a strong case. However, first-time arb salaries are based on a player’s entire career to that point, unlike second- and third-time arb salaries which are based more on a player’s most recent season. With the agents likely touting an elite platform season and the team likely pointing to earlier seasons to drive the cost down, a multi-year contract might be worth examining. Pittsburgh would get cost certainty, while Harrison would receive financial security in the event that he does not replicate his brilliant 2014.

Of course, from the Pirates’ point of view, they may look at Harrison as a player whose most consistent attributes are defense and baserunning — two aspects that, while valuable, are not highly rewarded in arbitration. While he does have a career-high in homers, the Pirates could also look to Harrison’s average fly-ball distance of 279.98 feet — 136th in the Majors according to BaseballHeatMaps.com — and the fact that seven of his 13 homers fall into the “just enough” category on ESPN’s Hit Tracker. Those two stats suggest that he may have difficulty sustaining this level of power, which would subsequently deflate his arb prices in future cases. A low-payroll team like the Pirates may express hesitancy at over-committing in the event that his power numbers won’t stay this high.

As such, Harrison and the Pirates may have trouble reaching common ground should either side look to pursue a long-term deal that buys out free agent years. The Pirates will cite Harrison’s short track record and reliance on defense and baserunning to provide value. Harrison’s agents, meanwhile, will likely position him as a breakout player and could point to five- or six-year pacts signed by other infielders in the past year or so. However, even a similar late bloomer like Matt Carpenter had an excellent 2012 season and a fourth-place MVP finish in 2013 before signing his six-year, $52MM contract. Harrison has just one elite season.

While Harrison isn’t the first player to jump from utility player to All-Star (though the feat certainly isn’t common), few, if any players have found themselves in his situation and his service bracket and ultimately inked a long-term deal. A look at extensions for infielders with three to four years of service time shows few deals that serve as comparables. Pablo Sandoval signed a three-year, $17.5MM to buy out his arb years at the same stage of his career, but he had a much better offensive profile at that point. Elvis Andrus‘ original three-year, $14.4MM extension was signed when he had an even three years of Major League service. He lacked an offensive season in the vein of Harrison’s excellent 2014, but he had a longer track record of providing value.

The Pirates are one of baseball’s most cost-conscious teams, and as such there would seem to be some benefit to securing Harrison’s arbitration paydays, and for a player with no track record prior to 2014, I’d think that holds some appeal to him as well. Perhaps the two sides could work out a three-year deal in the $15-16MM range to provide Harrison with a lifetime of financial security but still position him to hit free agency at a relatively young age in search of a significant payday. While Pittsburgh would undoubtedly have interest in adding a club option that could push the total value of the contract into the Michael Brantley range (four years, $25MM) if exercised, that doesn’t seem to be a worthwhile trade-off for player and agent, even if the buyout was fairly significant.

Beyond Harrison’s three arbitration years, the situation feels to this writer like one in which the team’s lack of margin for error (due to payroll constraints) makes betting on Harrison’s surprise breakout a bit too risky to pay him like the late-blooming star he could very well be. Of course, there’s risk for the team to pass on a long-term deal as well; if Harrison is capable of sustaining something close to this level of production, his price tag on a long-term deal a year from now could exceed that of Carpenter.

The Angels’ farm system hasn’t won much praise recently, but it seems to have produced a hit in Kole Calhoun. The outfielder sped through the minors despite a relatively modest pedigree (he was an eighth-round pick as a college senior in 2010), skipping Double-A and making it to the big leagues in two years. Last season, in his first extended shot in the Majors, he hit .282/.347/.462 in 222 plate appearances, and this year he’s proven that was no fluke, hitting .294/.349/.485 so far. Offensively, Calhoun combines high batting averages with good power, and he also provides reasonable baserunning and corner outfield defense.

Since he’s already nearly 27, Calhoun’s opportunities to cash in on his early-career success might be somewhat limited. He can’t become a free agent until the 2019-2020 offseason, by which point he’ll be 32. With so much time remaining before free agency, and after receiving a very modest $36K signing bonus out of college, it would probably behoove Calhoun to consider the security of a long-term deal. A pre-free agency extension might represent the best chance for Calhoun and his agent, Page Odle, to land a big contract.

Given that the Angels already control what are likely to be Calhoun’s prime years, an extension need not be such a priority for them. And since he isn’t exceptionally athletic and already plays corner outfield, betting on him continuing to be productive well into his thirties seems excessive, from the Angels’ perspective. Signing Calhoun to an extension would, however, have the benefit of controlling his arbitration salaries while possibly also giving the Angels options to control a year or two more than they do now.

Since Marte is an outfielder, his six-year, $31MM deal (which also includes two options) is the most obvious precedent that might guide a long-term deal for Calhoun. Before that, the last extensions for outfielders with between one and two years of service time were those of Jose Tabata (2011) and Denard Span (2010). Both contracts are now too ancient to really matter, with contracts for players like Simmons and Freddie Freeman reshaping the extension landscape since then.

The problem with using Marte’s deal as a precedent, though, is that a Calhoun contract would have a slightly different purpose. Marte was a toolsy, high-upside 25-year-old at the time of his deal, so for the Pirates, his contract was about retaining him long term. Calhoun is older and may have already reached his upside. On the other hand, his offense-heavy profile is more likely than Marte’s was to get him paid in arbitration. Therefore, we might expect a Calhoun contract to be a bit shorter than Marte’s, and perhaps a bit less option-heavy. We might also expect Calhoun to make more than Marte in his seasons of arbitration eligibility.

The possibility of Calhoun becoming a Super Two player following the 2015 season is also a factor. Calhoun entered the 2014 season with 130 days of service. This year’s projected Super Two threshold is two years and 128 days of service time, which means Calhoun could end up on either side of the line. Quintana had one year and 133 days of service when he signed his extension before the season, and his contract with the White Sox contains a clause that pays him an extra $5.5MM if he becomes Super Two eligible. Perhaps a Calhoun extension could include a similar clause.

Of course, Super Two eligibility would not affect Calhoun’s free agency timeline. A five-year deal (beginning in 2015) with one team option might make sense for both Calhoun and the Angels — such a deal would buy out all of Calhoun’s pre-free-agency seasons while giving the Angels the rights to his first season of free agency eligibility. Calhoun would become eligible for free agency as a 33-year-old at the latest, potentially giving him another shot at a multi-year deal if he continued to hit.

Given that the Angels already control one or perhaps two of those five years at the league minimum, the total guaranteed figure for a Calhoun extension need not be huge. Marte will make $21MM over the course of his contract if one leaves aside the last guaranteed year (including his signing bonus and a $2MM buyout on his option in 2020). Calhoun might get a little more than that guaranteed over a five-year deal if he is not Super Two eligible (including a buyout on the Angels’ option for a sixth year), perhaps with a clause bumping his contract to $27MM-$30MM if it turns out he is.

The Indians have been active in locking up top young players where possible, with Jason Kipnis, Michael Brantley, and Yan Gomes all receiving lengthy guarantees this spring in exchange for cost savings to the club. But the organization has been much stingier with promising dollars to pitchers. Most recently, the team declined to act on the seemingly reasonable demands of Justin Masterson over the past offseason (before ultimately dealing him away this summer). According to MLBTR’s Extension Tracker, the last time Cleveland promised future money to a big league hurler, Roberto Hernandez was still known as Fausto Carmona. Indeed, he was the last arm to receive an extension from the Indians, way back in April of 2008.

That track record suggests that, as aggressive as the Indians have been in making investments in position players, the club has been wary of doing so with inherently injury-prone pitchers. But whatever risk the team builds into its internal models, at some point it makes sense to pursue a deal. That is especially true when unique bargaining leverage might be had, as the player might be more inclined to take a relatively modest guarantee rather than rolling the dice on his own health.

The reason for that lengthy introduction? The team’s current ace, Corey Kluber. Where does the righty stand on the year? 2.46 ERA over 171 2/3 innings. 9.8 K/9 against 1.9 BB/9, 49.7% groundball rate. 2.43 FIP, 2.69 xFIP, 2.70 SIERA. 5.2 fWAR, 5.2 rWAR. 28 years old. Expected service time at end of 2014 season: 2.074, good for a first run at arbitration in 2016.

Put simply, these are the kinds of circumstances where an extension could make sense for both sides. Cleveland will no doubt be content letting Kluber go out and prove his worth year-to-year, comforted by the fact that he is controlled through his age-32 season. But arbitration can get expensive, and cost limits (as well as cost certainty) might be attractive. The club’s future commitments drop off after 2016, when the Nick Swisher and Michael Bourn deals are up, leaving plenty of space to add some guaranteed dollars. (As things stand, Cleveland has promised just $18.742MM of salary for 2017.)

Meanwhile, for Kluber, a substantial future guarantee would seem to represent a major attraction. As good as he’s been, he had thrown just over 200 MLB innings coming into the season. His strikeout and walk rates are each better now than they ever were over a full minor league season. As a fourth-rounder back in 2007, he was not a bonus baby. And he is still more than a full season away from being paid a fraction of his actual value through arbitration — let alone reaching the open market. And even then, his advanced age would be a major factor. (I looked at the situation of James Shields a few months back, concluding that he would struggle to reach five years at a $20MM AAV in free agency when he hits the market in advance of his age-33 season.) In many respects, Kluber’s situation is not unlike that of the late-blooming Josh Donaldson, with the major difference that Kluber’s earning capacity depends upon the health of a right arm that is subject to immense strain on a daily basis.

What kind of deal might make sense for team and player? It is difficult to find a direct comparable, given Kluber’s rather unique, suddenly-emergent excellence. Kluber’s value is undeniable: he landed at 42nd on Dave Cameron’s list of the game’s most valuable players. But even apart from his poor bargaining position, his age is a major limiting factor on his ability to command big dollars well into the future.

The most recent extension for a 2+ service time starting pitcher was given to Chris Sale of the White Sox before the 2013 season. Sale received a five-year, $32.5MM deal with two option years — the latest example of an oft-copied extension model. (Somewhat notably, Kluber is represented by Jet Sports Management, according to Baseball-Reference, the agency that negotiated Sale’s contract as well as the recent Charlie Morton extension.) More recently, Julio Teheran was able to command $32.4MM over six years from the Braves, while giving up one option year, despite being a year behind on service time.

Those deals guaranteed at least one free agent year, and Cleveland may not be interested in promising any cash for Kluber’s age-33 season. Might the Indians look to promise four years while obtaining two or even three options at a similar guarantee to those contracts? Could the team look to shave something off of the dollars in those packages, possibly in return for reduced future control? Presumably, the key motivation for the team would not be to extend control, but rather to achieve significant cost savings. There are plenty of possibilities, and creative strategies abound to create a fit.

As usual, a motivated club would be the key to striking a deal. Cleveland is in an enviable position with respect to Kluber, who is producing like an in-prime ace (with the peripherals to match) but doing so for a pittance. That situation also brings the temptation of reaching an even better bargain. And surely Kluber’s camp would have to listen hard to any possibilities of signing up for a life-setting payday that might otherwise require plenty more hard work and good luck to achieve. Needless to say, it would be an intriguing storyline to track if either side looks to kick-start offseason negotiations.

In May 2013, Pedro Alvarez's agent, Scott Boras, declared that he and his client would be "open" to the possibility of a long-term contract with the Pirates. Since then, and particularly since the Bucs inked Starling Marte to a long-term deal last month, the Pittsburgh media has chattered about the Pirates' chances of signing Alvarez.

That Boras was open to an Alvarez extension wasn't that surprising. Boras' antipathy to pre-free agent deals, or perhaps the impact of his antipathy to pre-free agent deals upon actual negotiations, is sometimes overstated — a number of Boras clients, including Carlos Gonzalez, Carlos Gomez, Carlos Pena, Elvis Andrus, Jered Weaver and Ryan Madson, have signed them. (Besides, Alvarez was hitting just .200/.257/.406 at the time of Boras' comments.)

Nonetheless, that Boras is Alvarez's agent is still an issue. Alvarez himself would probably have to be strongly in favor of a deal for Boras to sign off on it. The squabbles between Boras and the Pirates after the Bucs drafted Alvarez in 2008 might be anecdotal evidence that neither Boras nor Alvarez will cede much ground on an extension (although 2008 was also long enough ago that it might not matter). And Boras recently criticized "donut contracts" for pre-free agency players that feature options at the end. It probably would not be easy at all for the Pirates to work out a long-term deal for Alvarez.

Alvarez is set to make $4.25MM this year, his first year of arbitration eligibility, and to become eligible for free agency following the 2016 season. Pittsburgh Tribune-Review beat writer Travis Sawchik has frequently compared Alvarez's career to that of Chris Davis, and if Alvarez's age-27 season were to go as well as Davis' did, Alvarez would get enormous raises in his last two arbitration seasons — Davis, for example, got a raise from $3.3MM to $10.35MM after hitting 53 home runs last year. Still, a 50-homer season isn't likely for Alvarez, and arbitration salaries are broadly predictable, so let's guess that Alvarez will make about $22-25MM from 2014 through 2016 if the Pirates don't sign him long-term. (A $22MM-$25MM projection suggests he will still get fairly steep raises, given that power tends to be rewarded in arbitration.)

A long-term deal for Alvarez would likely start there. Where it would end up is another matter, and Freddie Freeman's enormous eight-year, $135MM contract with the Braves would be a very tough precedent for the Pirates to get around, given that both Freeman and Alvarez are both corner sluggers with between three and four years of service time. The Pirates might argue that Freeman is two-and-a-half years younger than Alvarez, and has a much better track record hitting for average. But even if we lop the last two years off Freeman's contract to address the age difference, we're left with six years and $91MM, which would be a lot for the Pirates to pay Alvarez, given that his next three seasons will be relatively cheap. Dropping that $91MM total somewhat to reflect Freeman's broader base of offensive skills would only help so much.

And even that might concede too much for Boras' taste. While Freeman is a better player than Alvarez, Boras might not see it that way, perhaps arguing that Alvarez's superior power ought to make him every bit as valuable to the Pirates as Freeman was for the Braves.

At this point, we're left with the question of just what a pre-free agency extension for Alvarez would be for. Alvarez is already 27, and the Pirates control him through his age-29 season. The only point in signing Alvarez long-term would be to control seasons beyond that, and Alvarez and Boras would surely want to be paid quite well to give up those seasons.

The problem is that it's not clear how valuable Alvarez will be in his thirties. His raw power is outstanding, on par with Davis', but only so much of Alvarez's raw power is usable, because of his struggles with strikeouts (he whiffed at least 180 times in both 2012 and 2013) and hitting for average. The track records of sluggers with serious strikeout issues are spotty — Mark Reynolds, for example, was productive while striking out prodigiously in his mid-twenties, but he hasn't had a truly strong offensive season since age 27. Ryan Howard's career and contract provide more cautionary tales. Alvarez's low averages (he's only hit above .244 once in his career) are already a concern. His plate appearances so far in 2014 have looked much better than in years past, so perhaps there's a faint possibility that Alvarez can master his strikeout issues. Unless he can prove himself over a longer time frame, however, it makes little sense to bet on that.

Then there are Alvarez's other skills. He's become an average third baseman and baserunner, but it's questionable whether he'll be able to maintain his current defensive and baserunning abilities as he heads into his thirties, given his bulky physique and lack of raw speed.

Given the likelihood that Alvarez won't age well, then, the Pirates' best course of action may simply be to enjoy the three years of him they have left. Signing a big, strikeout-prone slugger into his thirties doesn't make sense, even accounting for the slim possibility that he'll break out and become the next Chris Davis. Long-term contracts are calculated risks, and other things being equal, it's better to take the risk on a younger, more athletic player like Marte.

Second baseman Jason Kipnis and the Indians discussed the possibility of an extension last spring, but put those talks on hold when the 2013 season began. This year, Kipnis is again open to discussing an extension, as Paul Hoynes of the Plain Dealer reports. "Absolutely," Kipnis said when asked whether he would consider a multiyear deal. "We haven’t talked about it yet. My guess is if we started it would probably start in spring training when everyone reports. I think they have their hands full with arbitration cases right now."

Kipnis is the Indians' best player, and there are few holes in his offensive game. He hits for excellent power for a middle infielder, draws plenty of walks, and adds value on the bases. There's every reason to expect him to continue to be productive for the next few seasons. Those are seasons the Indians already control, however, which might make it tricky to negotiate a long-term deal with his representatives at Beverly Hills Sports Council.

Kipnis has 2.069 years of service time and will become arbitration-eligible next winter. He's eligible for free agency after 2017, which is his age-30 season. According to MLBTR's Extension Tracker, no second baseman with between two and three years of service time has signed an extension since Ben Zobrist in 2010. Expanding the field to include shortstops and third basemen doesn't yield many particularly revealing comparables, either, although Alexei Ramirez's four-year, $32.5MM contract, signed prior to the 2011 season, comes close. The deal did not kick in until 2012, however, which would have been Ramirez's second year of arbitration eligibility. Kipnis won't hit arbitration for the second time until two years from now.

To fashion a possible extension for Kipnis, let's look at recent arbitration cases to see what Kipnis might make in the 2015 through 2017 seasons. Via MLBTR's 2013 Arbitration Tracker, here are last year's arbitration results for players with between three and four years of service time. One that stands out is Ian Desmond, a shortstop who had been less consistent than Kipnis through that point in his career, but who had a similarly broad package of hitting and baserunning skills. Desmond made $3.8MM in his first year of arbitration eligibility. Neil Walker, another broadly-similar player, made $3.3MM, although that was as a Super Two.

Our starting point for Kipnis' 2015 season probably ought to be somewhat higher than Desmond's $3.8MM for 2013, compensating for Kipnis' greater consistency. If we guess that Kipnis might make $4.4MM in his first year of arbitration eligibility next winter, then he might make a total of about $20MM in his three arbitration seasons. Add in the $500K or so Kipnis is set to make this season, and we have a basic framework for an extension. The Indians might want to add in another guaranteed year, perhaps including an option. That might bring the total to something like five years and around $30MM-$35MM.

The main reason teams like pre-free agency extensions, however, is because they can control players beyond when they would have previously been eligible for free agency. How valuable Kipnis' free agent seasons will be, though, remains to be seen. Kipnis didn't debut until he was 24, and isn't eligible for free agency until he's about to turn 31.

Baseball history is filled with examples of good second basemen who faded quickly and/or at relatively young ages, including Edgardo Alfonzo, Brian Roberts, Jose Vidro, Chuck Knoblauch and former Indians great Carlos Baerga. Second basemen have to deal with hard slides around the bag, and because many of them (including Kipnis, who played shortstop in high school) are converted shortstops, they often don't represent the best athletes to begin with. Those concerns probably don't apply quite as readily to truly elite second basemen, as Dave Cameron of Fangraphs points out. That's one reason the Mariners and Red Sox have been willing to pay big bucks for Robinson Cano and Dustin Pedroia's thirty-something seasons. But Kipnis isn't in that category.

There is no reason for Kipnis to agree to an extension at a steep discount, either — he's only one season away from arbitration eligibility, and if he continues to produce, hitting free agency at age 30 rather than age 31 or 32 could make a significant difference in his first contract on the open market. Even though Kipnis is a star, then, the Indians could simply decide to take him year-to-year for now. They already control what are likely to be his prime years, and have limited leverage to get him to sign away seasons beyond 2017.